The Ins and Outs of the Upper East Side
by Chair4vr
Summary: This is a story told from the viewpoints of the ultimate insider and the newest outcast. Vanessa shows up to school to discover a world of lies and betrayal while making friends with unlikeliest of people: Constance's Queen B. N/B/C & S/D/V


_So this is a brand new fic I thought of yesterday, it will go back and forth between Blair's POV and Vanessa's as you learn about scandals and secrets imbedded in the lives of these UES teenagers. I'm going to use a lot of the elements from the original storyline with a few of my own choices. I hope you enjoy!_

Chapter 1: New Girl, New School

Vanessa had always been confident. She never used to second-guess herself, but that was because she knew she fit in. At public school in Boston everything made sense, she had gotten to know all the kids, she knew how to act, and how to dress. As she tried on her knew Constance uniform she couldn't help, but feel like she was looking at another person. Why her mother had decided that for her senior year their family should move back to New York, and Vanessa should have to go to a private school she would never understand. The only good thing that had come out of this was that she would finally get to go to school with her best friends, Jenny and Dan, though she thought of Dan as more than a friend. Vanessa hadn't seen them since she moved away two years ago.

She had decided to straighten her hair for school, normally she wore it in long curls, but Jenny had told her under no uncertain terms was she to wear her hair curly. When Vanessa asked why, Jenny had said it was for the best.

She was late, by the time she called Dan, he and Jenny had already left. Vanessa hopped on the bus and headed over to Manhattan, an alien planet where nothing made sense. As she walked up to the entryway of Constance she saw Jenny waiting for her.

"Hey, sorry I missed you guys." Vanessa said upon greeting the small blonde.

"No problem, it was good I got here early so I could arrange to be you tour guide for the Welcome Committee!"

"Ok, well where do we start? Hallway, classes, cafeteria?"

"If you value your reputation you will never go to the cafeteria." Vanessa was surprised by how serious Jenny sounded.

"Why?"

"Because cool people don't go there, they just don't."

"Since when do I care what the cool people do or don't do? For that matter when did you start caring?"

"Vanessa, at your old school the biggest concern was not getting stabbed. Here being popular is the most important thing. You're already at an instant disadvantage because you live in Brooklyn like Dan and me. I spent all of last year working my butt off to get onto the met steps."

"What does that even mean?"

"Its where they hang out, where anyone who matters sits."

"That's really shallow Jenny. Dan doesn't care about popularity."

"Well Dan lucked out and started dating Serena so he doesn't even need to try." Jenny pouted.

"Who's Serena?" Dan had told her he was seeing someone when she moved back, but she hadn't had the nerve to ask whom.

"Oh my god, you have so much you need learn if you want to fit in here. Serena is like one of the most popular girls in school. I need to give you a serious Gossip Girl tutorial after school!"

"Gossip Girl?"

"I don't even know how to respond to that." Jenny said dumbfounded.

"This is ridiculous. I'm not going to change who I am or do anything differently because a group of superficial snobs might not like me…" Vanessa was cut-off by Jenny grabbing her arm and jerking her out of the way.

"You need to stop blocking the hallway." She said under her breath.

"What? Why?" Jenny subtly pointed down the hallway. Vanessa turned her head to see every other girl was standing flat against a locker. The chatter that had once filled the hallways had quieted to a soft murmur as a group of girl emerged around the corner. They walked in a 'V' formation. On the ends trailed a tall African-American girl with black straight hair and a pretty Asian girl with bangs. They wore matching jackets and headbands. Next in the flanks were a short blonde with a bob and unreasonably short skirt, and a statuesque brunette with tan skin. They too both wore brightly colored headbands. In the center leading the pack was a petite brunette with porcelain skin and ruby red lips. Unlike the others she wasn't scowling at the other girls in the hallway. She looked bored more than anything; also unlike her minions she didn't wear any bright colors with her uniform. She looked like she had stepped out of an old movie from the forties. Everything about her screamed elegance and poise. Her dark curls swaying gently behind her navy headband as she walked down the corridor. When the girls reached Vanessa and Jenny the leader held up her hand to signal they were stopping and turned to Jenny.

She looked Vanessa up and down appraisingly then she turned to Jenny. "Who's your friend little J?" 'Little J was that Jenny's nick name here?' Vanessa pondered.

"Oh she's not my friend, I'm just giving her a tour." Jenny blurted, Vanessa recoiled slightly, her friend's words stinging her.

"Hm." Was all the tiny brunette offered before turning and leaving, her minions quickly following in suite.

"What the hell was that Jenny?" Vanessa demanded.

"I'm sorry, I just got kinda freaked out."

"Why? She just asked you who I was?"

"She's Blair Waldorf!" Jenny cried as if it explained everything, and if Vanessa had not been an outsider, new to this whole world it would have.

"Who is she? Everyone started acting all weird when she walked through."

"She is the most popular girl in school, and what she says goes, and who she doesn't like leaves. I have tried so hard to get on her good side I just didn't want to risk being dismissed."

"Dismissed? Do you hear yourself? You talk about that girl like she's a mob boss or something."

"No, she's way more powerful. Vanessa lets face it, you're not great at first impressions, and you're kind of preachy. If she doesn't like you and she knows we're friends… Its guilty by association."

"So I'm supposed to pretend to be someone I'm not and kiss the ass of a girl I don't even know just so you can be seen in public with me?" Vanessa asked incredulously.

"Kind of." Jenny said meekly.

"I'm not doing that Jenny, and neither should you. You're better than this."

"You don't get it." Jenny sighed in frustration. "I have to go, I can't be late for the steps."

"Jenny?"

"I'm sorry. I have to go." Jenny turned and hurried off towards the Met.

Vanessa headed into an open area that joined Constance Billard with St. Judes. She walked through the archway and spotted Dan. Unfortunately he was wrapped around a tall blonde.

"Hey" Vanessa said timidly as she approached the lovers. Dan tore his lips away from the girl, Vanessa assumed was Serena to look at her.

He smiled, "Hey Vanessa, sorry we didn't wait for you. Jenny wanted to get here early."

"Probably didn't want to risk walking into school with me." Vanessa said bitterly. Dan looked at her confused, but didn't ask.

"I wanted to introduce you guys when you first came back, Vanessa this is Serena, my girlfriend."

"Hi." Vanessa said, forcing the words to sound light-hearted.

"Hey, its great to meet you. Dan's told me all about you." She smiled, reaching out and pulling Vanessa into a hug. "Oh hey do you know what time it is?" she asked after releasing Vanessa.

"Umm, its almost 8." Dan answered.

"Ok, shoot I gotta go, Blair's waiting for me. Hey you should come buy the steps at lunch it'll be fun." Vanessa merely smiled at the suggestion, no way in hell it would happen. Serena quickly turned and left, her golden locks swaying in the breeze as the left.

"So your girlfriend is one of Blair's little minions too? I should have suspected, Jenny just gushed about how popular she was."

"Serena is not one of Blair's minions, they're friends."

"Like those headband wearing freaks are her friends? They follow her around like she's their god."

"It's sad how not far off you are." Dan chuckled.

"When did your sister become a social climbing robot?"

"When she came to Constance." He laughed, "Jenny just wants to fit in. At least this way she has Serena to look out for her. It's kinda nice,"

"No its not, you should have seen the way Jenny cowered down to this girl in the hall. She was one second away from falling to her knees and praying at the girl's Manoalos."

"Look I'm not saying I approve of how much Jenny wants to be apart of that group, but I can't change it. Was your run-in with Blair that bad? What did you do make eye-contact?"

"She didn't even speak to me, she spoke to _Jenny_ about me like I wasn't even there. I was ten seconds away from calling her out on it." Vanessa ranted.

"Don't. Blair is a firm believer in speaking when spoken to. She can make life at school really miserable for you. I'd go to lunch and make nice, Serena will have your back."

"Good, she'll be able to pull out the knife Jenny stuck in it."

"Don't you think you're over-reacting?"

"No." The five-minute bell sounded.

"I'll have Serena put in a good word for you, Blair can be a total bitch, but its better to just put up with it." He said as he grabbed is backpack.

"I can't believe this. What happened to the independent Humphreys' I knew and loved?"

"They were forced to go to this monarchist hell hole. Trust me, you get used to it." He called over his shoulder. Vanessa took out her schedule to find her first class, already regretting ever agreeing to move back.

_Feedback and Reviews are always wanted!_


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